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US 11,778,893 B2Granted
Indaceno derivatives as organic semiconductors
AssigneesClap Co., Ltd., King Abdullah University of Science and Technology
InventorsDaniel Kaelblein, Pascal Hayoz, Hu Chen, Iain McCulloch
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds comprising at least one unit of formula (1) or (1′) as well as a process for the preparation of the compounds, intermediates of this process, electronic devices comprising the compounds, and the use of the compounds as semiconducting materials.
Claims14
Compounds comprising at least one unit of formula
- wherein
- M1 and M2 are independently of each other an aromatic or heteroaromatic monocyclic or bicyclic ring system;
- X is at each occurrence O, S, Se or Te,
- Q is at each occurrence C, Si or Ge,
- R1 is at each occurrence selected from the group consisting of H, C1-50-alkyl, —[CH2]o—[O—SiRaRa]p—OSiRaRaRa, —[CH2]o—[RaRaSi—O]p—SiRaRaRa, —[CRbRb]q—CRbRbRb, C2-50-alkenyl, C2-50-alkynyl, C5-8-cycloalkyl, C6-14-aryl and 5 to 14 membered heteroaryl,
- wherein
- is an integer from 0 to 10,
- p is an integer from 1 to 40,
- Ra is at each occurrence C1-10-alkyl, C2-10-alkenyl or C2-10-alkynyl,
- q is an integer from 1 to 50,
- Rb is at each occurrence H or halogen, with the provisio that not all Rb in —[CRbRb]q—CRbRbRb are H,
- C1-50-alkyl, C2-50-alkenyl and C2-50-alkynyl can be substituted with one to four substituents independently selected from the group consisting of ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRc, NRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)Rc], SRc, CN, —SiRcRcRc and NO2,
- C5-8-cycloalkyl can be substituted with one or two substituents independently selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRc, NRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)Rc], SRc, halogen, CN, —SiRcRcRc and NO2;
- and one CH2-group of C5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NRc or NRc—CO,
- C6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to three substituents independently selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRcNRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)Rc], SRc, halogen, CN, and NO2,
- wherein
- Rc is at each occurrence H, C1-20-alkyl, C2-10-alkenyl or C2-10-alkynyl,
- R2 is at each occurrence H, C1-30-alkyl, C2-30-alkenyl or C2-30-alkynyl or halogen,
- n is 0, 1, 2, 3 or 4,
- m is 0, 1, 2, 3 or 4,
- and
- L1 and L2 are independently from each other and at each occurrence selected from the group consisting of C6-26-arylene, 5 to 20 membered heteroarylene,
- wherein
- C6-26-arylene and 5 to 20 membered heteroarylene can be substituted with one to four substituents Rd at each occurrence selected from the group consisting of H, C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl and halogen, and
- and can be substituted with one or two substituents at each occurrence selected from the group consisting of Re, COORe and CN, wherein Re is at each occurrence selected from the group consisting of H, C1-30-alkyl, C2-30-alkenyl and C2-30-alkynyl.
22 more elements
Compounds of formula
- wherein
- M1 and M2 are independently of each other an aromatic or heteroaromatic monocyclic or bicyclic ring system;
- X is at each occurrence O, S, Se or Te,
- Q is at each occurrence C, Si or Ge,
- R1 is at each occurrence selected from the group consisting of H, C1-50-alkyl, —[CH2]o—[O—SiRaRa]p—OSiRaRaRa, —[CH2]o—[RaRaSi—O]p—SiRaRaRa, —[CRbRb]q—CRbRbRb, C2-50-alkenyl, C2-50-alkynyl, C5-8-cycloalkyl, C6-14-aryl and 5 to 14 membered heteroaryl,
- wherein
- is an integer from 0 to 10,
- p is an integer from 1 to 40,
- Ra is at each occurrence C1-10-alkyl, C2-10-alkenyl or C2-10-alkynyl,
- q is an integer from 1 to 50,
- Rb is at each occurrence H or halogen, with the provisio that not all Rb in —[CRbRb]q—CRbRbRb are H,
- C1-50-alkyl, C2-50-alkenyl and C2-50-alkynyl can be substituted with one to four substituents independently selected from the group consisting of ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRc, NRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)Rc], SRc, CN, —SiRcRcRc and NO2,
- C5-8-cycloalkyl can be substituted with one or two substituents independently selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRc, NRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)R], SRc, halogen, CN, —SiRcRcRc and NO2;
- and one CH2-group of C5-8-cycloalkyl can be replaced by O, S, OC(O), CO, NRc or NRc—CO,
- C6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one to three substituents independently selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, ORc, OC(O)—Rc, C(O)—ORc, C(O)—Rc, NRcRc, NRc—C(O)Rc, C(O)—NRcRc, N[C(O)Rc][C(O)Rc], SRc, halogen, CN, and NO2,
- wherein
- Rc is at each occurrence H, C1-20-alkyl, C2-10-alkenyl or C2-10-alkynyl,
- R2 is at each occurrence H, C1-30-alkyl, C2-30-alkenyl or C2-30-alkynyl or halogen.
15 more elements
Dependencies are inferred from the claim text.